A novel class of potential herbicides, the 3-(methoxycarbonylmethylene) isobenzofuran-1-imines, has been discovered. The herbicidal activity has been tested on two particular molecules, (E)-methyl 2-[3-(butylimino)isobenzofuran- 1(3H)-ylidene]acetate (1) and (E)-methyl 2-phenyl-2-[3-(phenylimino) isobenzofuran-1(3H)-ylidene]acetate (2), prepared by palladium-catalyzed oxidative carbonylation of 2-alkynylbenzamides. Both compounds 1 and 2 showed a strong phytotoxic effect on both shoot and root systems of Arabidopsis thaliana. The effects observed on the shoot were similar for both molecules, but while compound 1 showed a stronger effect on root parameters (such as primary root length, root hair and density, showing lower ED50 values), compound 2 caused important malformations in root morphology. Our results indicate that these molecules are very promising synthetic herbicides.

3-(Methoxycarbonylmethylene)isobenzofuran-1-imines as a new class of potential herbicides / F. Araniti, R. Mancuso, I. Ziccarelli, F. Sunseri, M.R. Abenavoli, B. Gabriele. - In: MOLECULES. - ISSN 1420-3049. - 19:6(2014), pp. 8261-8275. [10.3390/molecules19068261]

3-(Methoxycarbonylmethylene)isobenzofuran-1-imines as a new class of potential herbicides

F. Araniti;
2014

Abstract

A novel class of potential herbicides, the 3-(methoxycarbonylmethylene) isobenzofuran-1-imines, has been discovered. The herbicidal activity has been tested on two particular molecules, (E)-methyl 2-[3-(butylimino)isobenzofuran- 1(3H)-ylidene]acetate (1) and (E)-methyl 2-phenyl-2-[3-(phenylimino) isobenzofuran-1(3H)-ylidene]acetate (2), prepared by palladium-catalyzed oxidative carbonylation of 2-alkynylbenzamides. Both compounds 1 and 2 showed a strong phytotoxic effect on both shoot and root systems of Arabidopsis thaliana. The effects observed on the shoot were similar for both molecules, but while compound 1 showed a stronger effect on root parameters (such as primary root length, root hair and density, showing lower ED50 values), compound 2 caused important malformations in root morphology. Our results indicate that these molecules are very promising synthetic herbicides.
Arabidopsis thaliana; Carbonylation; Isobenzofuranimines; Phytotoxicity; Root morphology; Shoot parameters
Settore AGR/13 - Chimica Agraria
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/865250
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